# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_V479
_database_code_depnum_ccdc_archive 'CCDC 1973260'
loop_
_audit_author_name
_audit_author_address
'Alexander Vasiliev'
;Institute of Physics, Krasnouarsk Scientific Center
Russia
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
dicarbonyl(4-pyridylethynyl)(η⁵-cyclopentadienyl)iron
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Fe N O2'
_chemical_formula_sum            'C14 H9 Fe N O2'
_chemical_formula_weight         279.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.9444(13)
_cell_length_b                   9.1089(7)
_cell_length_c                   17.4069(14)
_cell_angle_alpha                90
_cell_angle_beta                 114.1838(17)
_cell_angle_gamma                90
_cell_volume                     2450.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3249
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.11

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.221
_shelx_estimated_absorpt_T_min   0.523
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5912
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13414
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.565
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2678
_reflns_number_gt                2067
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker PHOTON 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+3.4496P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2678
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1134
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.35265(4) 0.51344(4) 0.53950(3) 0.0605(2) Uani 1 1 d . . . . .
C1 C 0.2386(3) 0.5035(4) 0.4922(3) 0.0734(11) Uani 1 1 d . . . . .
O1 O 0.1655(2) 0.4967(4) 0.4619(2) 0.1025(10) Uani 1 1 d . . . . .
C2 C 0.3599(3) 0.6487(4) 0.4704(3) 0.0770(11) Uani 1 1 d . . . . .
O2 O 0.3657(3) 0.7330(3) 0.4258(2) 0.1147(12) Uani 1 1 d . . . . .
C3 C 0.4543(3) 0.4040(5) 0.6358(3) 0.0830(13) Uani 1 1 d . . . . .
H3 H 0.481(3) 0.330(5) 0.626(3) 0.089(14) Uiso 1 1 d . . . . .
C4 C 0.3797(4) 0.3959(5) 0.6503(3) 0.0829(13) Uani 1 1 d . . . . .
H4 H 0.352(2) 0.327(4) 0.652(2) 0.076(12) Uiso 1 1 d . . . . .
C5 C 0.3558(3) 0.5407(5) 0.6600(3) 0.0797(12) Uani 1 1 d . . . . .
H5 H 0.306(2) 0.568(4) 0.666(2) 0.074(11) Uiso 1 1 d . . . . .
C6 C 0.4139(3) 0.6365(5) 0.6492(3) 0.0778(11) Uani 1 1 d . . . . .
H6 H 0.418(3) 0.739(5) 0.654(3) 0.104(15) Uiso 1 1 d . . . . .
C7 C 0.4757(3) 0.5514(5) 0.6338(3) 0.0823(12) Uani 1 1 d . . . . .
H7 H 0.522(2) 0.576(4) 0.630(2) 0.067(11) Uiso 1 1 d . . . . .
C8 C 0.3580(2) 0.3663(3) 0.4639(2) 0.0624(9) Uani 1 1 d . . . . .
C9 C 0.3611(2) 0.2745(4) 0.4155(2) 0.0635(9) Uani 1 1 d . . . . .
C10 C 0.3681(2) 0.1643(3) 0.3608(2) 0.0565(8) Uani 1 1 d . . . . .
C11 C 0.4432(3) 0.0838(4) 0.3805(3) 0.0668(10) Uani 1 1 d . . . . .
H11 H 0.486(2) 0.092(4) 0.428(2) 0.086(14) Uiso 1 1 d . . . . .
C12 C 0.4460(4) -0.0204(5) 0.3236(4) 0.0890(15) Uani 1 1 d . . . . .
H12 H 0.492(3) -0.058(5) 0.340(3) 0.100(18) Uiso 1 1 d . . . . .
C13 C 0.3122(4) 0.0248(6) 0.2342(3) 0.0891(14) Uani 1 1 d . . . . .
H13 H 0.267(2) 0.009(4) 0.192(2) 0.052(10) Uiso 1 1 d . . . . .
C14 C 0.3017(3) 0.1334(4) 0.2838(3) 0.0702(10) Uani 1 1 d . . . . .
H14 H 0.258(2) 0.186(4) 0.268(2) 0.055(11) Uiso 1 1 d . . . . .
N N 0.3823(3) -0.0524(4) 0.2520(3) 0.0915(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe C2 1.761(4) . ?
Fe C1 1.766(5) . ?
Fe C8 1.906(3) . ?
Fe C4 2.087(4) . ?
Fe C6 2.087(4) . ?
Fe C7 2.087(5) . ?
Fe C5 2.091(4) . ?
Fe C3 2.098(5) . ?
C1 O1 1.131(5) . ?
C2 O2 1.124(4) . ?
C3 C4 1.389(6) . ?
C3 C7 1.394(6) . ?
C3 H3 0.86(4) . ?
C4 C5 1.410(6) . ?
C4 H4 0.80(4) . ?
C5 C6 1.385(6) . ?
C5 H5 0.93(4) . ?
C6 C7 1.414(6) . ?
C6 H6 0.94(4) . ?
C7 H7 0.85(4) . ?
C8 C9 1.203(4) . ?
C9 C10 1.422(4) . ?
C10 C14 1.382(5) . ?
C10 C11 1.383(5) . ?
C11 C12 1.386(6) . ?
C11 H11 0.85(4) . ?
C12 N 1.304(7) . ?
C12 H12 0.79(4) . ?
C13 N 1.303(7) . ?
C13 C14 1.371(6) . ?
C13 H13 0.82(3) . ?
C14 H14 0.83(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Fe C1 94.98(19) . . ?
C2 Fe C8 89.07(16) . . ?
C1 Fe C8 89.68(17) . . ?
C2 Fe C4 160.1(2) . . ?
C1 Fe C4 100.86(19) . . ?
C8 Fe C4 102.89(16) . . ?
C2 Fe C6 95.82(17) . . ?
C1 Fe C6 119.55(18) . . ?
C8 Fe C6 149.64(18) . . ?
C4 Fe C6 65.88(18) . . ?
C2 Fe C7 95.44(19) . . ?
C1 Fe C7 157.67(18) . . ?
C8 Fe C7 110.18(18) . . ?
C4 Fe C7 65.63(19) . . ?
C6 Fe C7 39.59(17) . . ?
C2 Fe C5 128.47(17) . . ?
C1 Fe C5 92.68(19) . . ?
C8 Fe C5 141.91(16) . . ?
C4 Fe C5 39.44(16) . . ?
C6 Fe C5 38.73(16) . . ?
C7 Fe C5 65.46(19) . . ?
C2 Fe C3 127.9(2) . . ?
C1 Fe C3 137.01(18) . . ?
C8 Fe C3 87.82(17) . . ?
C4 Fe C3 38.78(17) . . ?
C6 Fe C3 65.59(18) . . ?
C7 Fe C3 38.91(18) . . ?
C5 Fe C3 65.18(18) . . ?
O1 C1 Fe 179.8(5) . . ?
O2 C2 Fe 178.4(4) . . ?
C4 C3 C7 108.7(4) . . ?
C4 C3 Fe 70.2(3) . . ?
C7 C3 Fe 70.1(3) . . ?
C4 C3 H3 125(3) . . ?
C7 C3 H3 126(3) . . ?
Fe C3 H3 122(3) . . ?
C3 C4 C5 107.4(4) . . ?
C3 C4 Fe 71.1(2) . . ?
C5 C4 Fe 70.4(2) . . ?
C3 C4 H4 131(3) . . ?
C5 C4 H4 122(3) . . ?
Fe C4 H4 122(3) . . ?
C6 C5 C4 108.6(4) . . ?
C6 C5 Fe 70.5(2) . . ?
C4 C5 Fe 70.1(2) . . ?
C6 C5 H5 126(2) . . ?
C4 C5 H5 126(2) . . ?
Fe C5 H5 120(2) . . ?
C5 C6 C7 107.6(4) . . ?
C5 C6 Fe 70.8(2) . . ?
C7 C6 Fe 70.2(3) . . ?
C5 C6 H6 130(3) . . ?
C7 C6 H6 122(3) . . ?
Fe C6 H6 128(3) . . ?
C3 C7 C6 107.7(4) . . ?
C3 C7 Fe 71.0(3) . . ?
C6 C7 Fe 70.2(3) . . ?
C3 C7 H7 121(3) . . ?
C6 C7 H7 131(3) . . ?
Fe C7 H7 130(3) . . ?
C9 C8 Fe 179.4(3) . . ?
C8 C9 C10 177.7(4) . . ?
C14 C10 C11 115.7(3) . . ?
C14 C10 C9 122.4(3) . . ?
C11 C10 C9 122.0(3) . . ?
C10 C11 C12 118.9(4) . . ?
C10 C11 H11 121(3) . . ?
C12 C11 H11 120(3) . . ?
N C12 C11 125.3(5) . . ?
N C12 H12 124(4) . . ?
C11 C12 H12 111(4) . . ?
N C13 C14 125.5(5) . . ?
N C13 H13 123(2) . . ?
C14 C13 H13 112(3) . . ?
C13 C14 C10 119.5(5) . . ?
C13 C14 H14 123(2) . . ?
C10 C14 H14 118(2) . . ?
C13 N C12 115.1(4) . . ?

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ant20
_database_code_depnum_ccdc_archive 'CCDC 1973917'
loop_
_audit_author_name
_audit_author_address
'Alexander Vasiliev'
;Institute of Physics, Krasnouarsk Scientific Center SB RAS
Russia
;
_audit_update_record             
;
2019-12-24 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
dicarbonyl(3-pyridylethynyl)(η⁵-cyclopentadienyl)iron
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Fe N O2'
_chemical_formula_sum            'C14 H9 Fe N O2'
_chemical_formula_weight         279.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4258(5)
_cell_length_b                   9.5785(5)
_cell_length_c                   13.8330(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.5340(10)
_cell_angle_gamma                90
_cell_volume                     1177.03(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2859
_cell_measurement_theta_min      2.302
_cell_measurement_theta_max      28.975

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.360
_exptl_absorpt_coefficient_mu    1.271
_shelx_estimated_absorpt_T_min   0.563
_shelx_estimated_absorpt_T_max   0.657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6196
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   
;
 Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15154
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.303
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3115
_reflns_number_gt                2287
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker PHOTON 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+0.2701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3115
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.0895
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.22995(4) 0.60833(3) 0.34868(2) 0.03322(11) Uani 1 1 d . . . . .
O1 O 0.0554(2) 0.6858(2) 0.14015(14) 0.0602(5) Uani 1 1 d . . . . .
O2 O 0.3785(2) 0.8765(2) 0.40484(16) 0.0616(6) Uani 1 1 d . . . . .
N N 0.6863(3) 0.5723(3) 0.0738(2) 0.0647(7) Uani 1 1 d . . . . .
C1 C 0.1234(3) 0.6569(3) 0.2223(2) 0.0399(6) Uani 1 1 d . . . . .
C2 C 0.3180(3) 0.7728(3) 0.38193(18) 0.0413(6) Uani 1 1 d . . . . .
C3 C 0.2779(4) 0.4395(3) 0.4518(2) 0.0583(8) Uani 1 1 d . . . . .
H3 H 0.3644 0.3849 0.4695 0.070 Uiso 1 1 calc R U . . .
C4 C 0.1449(4) 0.4146(3) 0.3706(2) 0.0570(8) Uani 1 1 d . . . . .
H4 H 0.1275 0.3414 0.3238 0.068 Uiso 1 1 calc R U . . .
C5 C 0.0420(3) 0.5202(3) 0.3723(2) 0.0534(7) Uani 1 1 d . . . . .
H5 H -0.0564 0.5282 0.3275 0.064 Uiso 1 1 calc R U . . .
C6 C 0.1121(3) 0.6102(3) 0.4522(2) 0.0526(7) Uani 1 1 d . . . . .
H6 H 0.0699 0.6897 0.4700 0.063 Uiso 1 1 calc R U . . .
C7 C 0.2587(3) 0.5599(3) 0.5016(2) 0.0565(8) Uani 1 1 d . . . . .
H7 H 0.3304 0.6004 0.5581 0.068 Uiso 1 1 calc R U . . .
C8 C 0.3852(3) 0.5542(3) 0.29525(18) 0.0371(5) Uani 1 1 d . . . . .
C9 C 0.4747(3) 0.5253(3) 0.25382(18) 0.0393(5) Uani 1 1 d . . . . .
C10 C 0.5763(3) 0.4942(3) 0.19900(18) 0.0372(5) Uani 1 1 d . . . . .
C11 C 0.6555(3) 0.3698(3) 0.2086(2) 0.0459(6) Uani 1 1 d . . . . .
H11 H 0.6476 0.3016 0.2544 0.055 Uiso 1 1 calc R U . . .
C12 C 0.7461(3) 0.3484(3) 0.1495(2) 0.0519(7) Uani 1 1 d . . . . .
H12 H 0.7987 0.2651 0.1543 0.062 Uiso 1 1 calc R U . . .
C13 C 0.7575(3) 0.4510(3) 0.0838(2) 0.0563(7) Uani 1 1 d . . . . .
H13 H 0.8183 0.4349 0.0440 0.068 Uiso 1 1 calc R U . . .
C14 C 0.5985(3) 0.5909(3) 0.1303(2) 0.0534(7) Uani 1 1 d . . . . .
H14 H 0.5476 0.6754 0.1234 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe C1 1.763(3) . ?
Fe C2 1.769(3) . ?
Fe C8 1.919(2) . ?
Fe C4 2.084(3) . ?
Fe C6 2.085(3) . ?
Fe C5 2.085(3) . ?
Fe C7 2.093(3) . ?
Fe C3 2.103(3) . ?
O1 C1 1.137(3) . ?
O2 C2 1.136(3) . ?
N C14 1.326(3) . ?
N C13 1.326(4) . ?
C3 C7 1.386(4) . ?
C3 C4 1.396(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.408(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.406(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.200(3) . ?
C9 C10 1.437(3) . ?
C10 C11 1.388(3) . ?
C10 C14 1.392(3) . ?
C11 C12 1.381(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.368(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Fe C2 94.87(11) . . ?
C1 Fe C8 86.82(11) . . ?
C2 Fe C8 89.35(11) . . ?
C1 Fe C4 105.07(12) . . ?
C2 Fe C4 157.78(12) . . ?
C8 Fe C4 101.27(11) . . ?
C1 Fe C6 114.90(12) . . ?
C2 Fe C6 97.20(11) . . ?
C8 Fe C6 156.49(11) . . ?
C4 Fe C6 65.71(11) . . ?
C1 Fe C5 91.73(11) . . ?
C2 Fe C5 132.02(12) . . ?
C8 Fe C5 138.51(12) . . ?
C4 Fe C5 39.49(12) . . ?
C6 Fe C5 38.72(11) . . ?
C1 Fe C7 154.04(12) . . ?
C2 Fe C7 92.51(12) . . ?
C8 Fe C7 118.16(11) . . ?
C4 Fe C7 65.27(12) . . ?
C6 Fe C7 39.32(11) . . ?
C5 Fe C7 65.23(11) . . ?
C1 Fe C3 142.92(13) . . ?
C2 Fe C3 122.19(12) . . ?
C8 Fe C3 92.00(11) . . ?
C4 Fe C3 38.96(12) . . ?
C6 Fe C3 65.40(12) . . ?
C5 Fe C3 65.39(12) . . ?
C7 Fe C3 38.56(12) . . ?
C14 N C13 116.8(2) . . ?
O1 C1 Fe 178.6(2) . . ?
O2 C2 Fe 177.9(2) . . ?
C7 C3 C4 108.1(3) . . ?
C7 C3 Fe 70.34(16) . . ?
C4 C3 Fe 69.76(16) . . ?
C7 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
Fe C3 H3 125.5 . . ?
C3 C4 C5 107.5(3) . . ?
C3 C4 Fe 71.27(16) . . ?
C5 C4 Fe 70.31(15) . . ?
C3 C4 H4 126.2 . . ?
C5 C4 H4 126.2 . . ?
Fe C4 H4 123.8 . . ?
C6 C5 C4 108.3(3) . . ?
C6 C5 Fe 70.63(15) . . ?
C4 C5 Fe 70.20(15) . . ?
C6 C5 H5 125.9 . . ?
C4 C5 H5 125.9 . . ?
Fe C5 H5 124.9 . . ?
C5 C6 C7 107.8(3) . . ?
C5 C6 Fe 70.64(15) . . ?
C7 C6 Fe 70.67(15) . . ?
C5 C6 H6 126.1 . . ?
C7 C6 H6 126.1 . . ?
Fe C6 H6 124.2 . . ?
C3 C7 C6 108.3(3) . . ?
C3 C7 Fe 71.10(16) . . ?
C6 C7 Fe 70.01(15) . . ?
C3 C7 H7 125.8 . . ?
C6 C7 H7 125.9 . . ?
Fe C7 H7 124.6 . . ?
C9 C8 Fe 174.3(2) . . ?
C8 C9 C10 176.8(3) . . ?
C11 C10 C14 115.9(2) . . ?
C11 C10 C9 124.0(2) . . ?
C14 C10 C9 120.1(2) . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
N C13 C12 123.3(3) . . ?
N C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
N C14 C10 125.4(3) . . ?
N C14 H14 117.3 . . ?
C10 C14 H14 117.3 . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.060

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_v477_a
_database_code_depnum_ccdc_archive 'CCDC 1973678'
loop_
_audit_author_name
_audit_author_address
'Alexander Vasiliev'
;Institute of Physics, Krasnouarsk Scientific Center SB RAS
Russia
;
_audit_update_record             
;
2019-12-23 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
dicarbonyl(2-pyridylethynyl)(η⁵-cyclopentadienyl)iron
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Fe N O2'
_chemical_formula_sum            'C14 H9 Fe N O2'
_chemical_formula_weight         279.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4756(2)
_cell_length_b                   9.7388(2)
_cell_length_c                   13.6391(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.8340(10)
_cell_angle_gamma                90
_cell_volume                     1191.24(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5131
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      30.47

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    1.256
_shelx_estimated_absorpt_T_min   0.540
_shelx_estimated_absorpt_T_max   0.633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6669
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16740
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.309
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3475
_reflns_number_gt                2754
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker PHOTON 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+0.2647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3475
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0821
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.22645(3) 0.39608(2) 0.34826(2) 0.03974(9) Uani 1 1 d . . . . .
N N 0.6445(2) 0.64460(19) 0.22143(17) 0.0685(5) Uani 1 1 d . . . . .
C1 C 0.31535(19) 0.2348(2) 0.38005(13) 0.0457(4) Uani 1 1 d . . . . .
O1 O 0.37492(18) 0.13300(16) 0.40245(12) 0.0666(4) Uani 1 1 d . . . . .
C2 C 0.1221(2) 0.34799(19) 0.22000(14) 0.0478(4) Uani 1 1 d . . . . .
O2 O 0.05732(17) 0.31937(17) 0.13716(11) 0.0670(4) Uani 1 1 d . . . . .
C3 C 0.2734(3) 0.5598(2) 0.45408(18) 0.0666(6) Uani 1 1 d . . . . .
H3 H 0.3605 0.6116 0.4727 0.080 Uiso 1 1 calc R U . . .
C4 C 0.2496(2) 0.4412(3) 0.50315(15) 0.0625(5) Uani 1 1 d . . . . .
H4 H 0.3181 0.4002 0.5605 0.075 Uiso 1 1 calc R U . . .
C5 C 0.1048(2) 0.3938(2) 0.45170(16) 0.0580(5) Uani 1 1 d . . . . .
H5 H 0.0609 0.3157 0.4684 0.070 Uiso 1 1 calc R U . . .
C6 C 0.0385(2) 0.4846(2) 0.37110(16) 0.0629(5) Uani 1 1 d . . . . .
H6 H -0.0581 0.4782 0.3251 0.075 Uiso 1 1 calc R U . . .
C7 C 0.1428(3) 0.5877(2) 0.37120(19) 0.0671(6) Uani 1 1 d . . . . .
H7 H 0.1280 0.6608 0.3250 0.081 Uiso 1 1 calc R U . . .
C8 C 0.38073(19) 0.45262(19) 0.29448(13) 0.0438(4) Uani 1 1 d . . . . .
C9 C 0.4728(2) 0.48426(19) 0.25500(14) 0.0467(4) Uani 1 1 d . . . . .
C10 C 0.57567(18) 0.52163(18) 0.20190(13) 0.0435(4) Uani 1 1 d . . . . .
C11 C 0.6031(3) 0.4307(3) 0.1339(2) 0.0753(7) Uani 1 1 d . . . . .
H11 H 0.5578 0.3448 0.1237 0.090 Uiso 1 1 calc R U . . .
C12 C 0.6970(4) 0.4672(3) 0.0815(3) 0.1024(11) Uani 1 1 d . . . . .
H12 H 0.7156 0.4057 0.0349 0.123 Uiso 1 1 calc R U . . .
C13 C 0.7637(3) 0.5908(3) 0.0957(2) 0.0771(7) Uani 1 1 d . . . . .
H13 H 0.8259 0.6167 0.0583 0.092 Uiso 1 1 calc R U . . .
C14 C 0.7375(3) 0.6761(3) 0.1661(2) 0.0761(7) Uani 1 1 d . . . . .
H14 H 0.7852 0.7609 0.1774 0.091 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe C1 1.7686(19) . ?
Fe C2 1.7721(19) . ?
Fe C8 1.9159(17) . ?
Fe C6 2.0903(18) . ?
Fe C7 2.091(2) . ?
Fe C5 2.0901(18) . ?
Fe C4 2.0989(18) . ?
Fe C3 2.100(2) . ?
N C10 1.349(2) . ?
N C14 1.367(3) . ?
C1 O1 1.133(2) . ?
C2 O2 1.133(2) . ?
C3 C4 1.389(3) . ?
C3 C7 1.407(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.204(2) . ?
C9 C10 1.436(2) . ?
C10 C11 1.366(3) . ?
C11 C12 1.357(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.344(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.352(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Fe C2 94.43(8) . . ?
C1 Fe C8 89.26(8) . . ?
C2 Fe C8 87.11(8) . . ?
C1 Fe C6 133.70(9) . . ?
C2 Fe C6 91.46(9) . . ?
C8 Fe C6 136.94(9) . . ?
C1 Fe C7 158.39(9) . . ?
C2 Fe C7 105.43(9) . . ?
C8 Fe C7 100.01(8) . . ?
C6 Fe C7 39.38(9) . . ?
C1 Fe C5 98.51(8) . . ?
C2 Fe C5 114.21(9) . . ?
C8 Fe C5 156.42(8) . . ?
C6 Fe C5 38.91(8) . . ?
C7 Fe C5 65.79(8) . . ?
C1 Fe C4 93.00(8) . . ?
C2 Fe C4 153.20(9) . . ?
C8 Fe C4 118.72(9) . . ?
C6 Fe C4 65.21(8) . . ?
C7 Fe C4 65.41(9) . . ?
C5 Fe C4 39.10(9) . . ?
C1 Fe C3 121.82(9) . . ?
C2 Fe C3 143.72(10) . . ?
C8 Fe C3 91.51(8) . . ?
C6 Fe C3 65.55(9) . . ?
C7 Fe C3 39.25(10) . . ?
C5 Fe C3 65.46(9) . . ?
C4 Fe C3 38.65(9) . . ?
C10 N C14 116.6(2) . . ?
O1 C1 Fe 178.29(17) . . ?
O2 C2 Fe 178.38(18) . . ?
C4 C3 C7 108.1(2) . . ?
C4 C3 Fe 70.65(12) . . ?
C7 C3 Fe 70.03(12) . . ?
C4 C3 H3 126.0 . . ?
C7 C3 H3 126.0 . . ?
Fe C3 H3 125.0 . . ?
C3 C4 C5 108.5(2) . . ?
C3 C4 Fe 70.70(11) . . ?
C5 C4 Fe 70.11(11) . . ?
C3 C4 H4 125.7 . . ?
C5 C4 H4 125.7 . . ?
Fe C4 H4 125.0 . . ?
C6 C5 C4 107.8(2) . . ?
C6 C5 Fe 70.55(10) . . ?
C4 C5 Fe 70.79(11) . . ?
C6 C5 H5 126.1 . . ?
C4 C5 H5 126.1 . . ?
Fe C5 H5 124.2 . . ?
C5 C6 C7 108.3(2) . . ?
C5 C6 Fe 70.54(11) . . ?
C7 C6 Fe 70.32(11) . . ?
C5 C6 H6 125.8 . . ?
C7 C6 H6 125.8 . . ?
Fe C6 H6 124.9 . . ?
C6 C7 C3 107.3(2) . . ?
C6 C7 Fe 70.30(11) . . ?
C3 C7 Fe 70.72(12) . . ?
C6 C7 H7 126.3 . . ?
C3 C7 H7 126.3 . . ?
Fe C7 H7 124.3 . . ?
C9 C8 Fe 175.94(16) . . ?
C8 C9 C10 176.54(19) . . ?
N C10 C11 121.57(17) . . ?
N C10 C9 119.29(17) . . ?
C11 C10 C9 119.14(17) . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 117.9(2) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C13 C14 N 123.6(2) . . ?
C13 C14 H14 118.2 . . ?
N C14 H14 118.2 . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.045

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ant19
_database_code_depnum_ccdc_archive 'CCDC 1982510'
loop_
_audit_author_name
_audit_author_address
'Alexander D. Vasiliev'
;Institute of Physics, Krasnouarsk Scientific Center SB RAS
Russia
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H8 Fe N2 O2 S'
_chemical_formula_sum            'C15 H8 Fe N2 O2 S'
_chemical_formula_weight         336.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.4302(5)
_cell_length_b                   11.8451(10)
_cell_length_c                   17.9823(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.765(2)
_cell_angle_gamma                90
_cell_volume                     1366.69(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2151
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      23.44

_exptl_crystal_description       prism
_exptl_crystal_colour            dark-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.260
_shelx_estimated_absorpt_T_min   0.607
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6461
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14867
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.060
_diffrn_reflns_theta_max         26.963
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2964
_reflns_number_gt                2227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker PHOTON II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.2917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2964
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.54770(7) 0.27329(4) 0.51452(2) 0.03574(16) Uani 1 1 d . . . . .
S S -0.29236(17) 0.27855(11) 0.24146(6) 0.0719(3) Uani 1 1 d . . . . .
O1 O 0.2841(4) 0.0741(2) 0.50313(15) 0.0619(7) Uani 1 1 d . . . . .
O2 O 0.2647(4) 0.4089(2) 0.59715(16) 0.0620(7) Uani 1 1 d . . . . .
N1 N -0.0804(5) 0.2843(3) 0.29411(16) 0.0494(7) Uani 1 1 d . . . . .
N2 N -0.2620(5) 0.3824(3) 0.18651(18) 0.0684(10) Uani 1 1 d . . . . .
C1 C 0.3887(5) 0.1522(3) 0.50835(18) 0.0425(8) Uani 1 1 d . . . . .
C2 C 0.3729(5) 0.3546(3) 0.56391(19) 0.0434(8) Uani 1 1 d . . . . .
C3 C 0.4129(5) 0.3252(3) 0.42259(18) 0.0412(8) Uani 1 1 d . . . . .
C4 C 0.8015(5) 0.3781(3) 0.5460(2) 0.0497(9) Uani 1 1 d . . . . .
H4 H 0.7909 0.4548 0.5563 0.060 Uiso 1 1 calc R U . . .
C5 C 0.8330(5) 0.3302(3) 0.4767(2) 0.0505(9) Uani 1 1 d . . . . .
H5 H 0.8495 0.3699 0.4328 0.061 Uiso 1 1 calc R U . . .
C6 C 0.8358(5) 0.2115(3) 0.4841(2) 0.0547(10) Uani 1 1 d . . . . .
H6 H 0.8518 0.1594 0.4463 0.066 Uiso 1 1 calc R U . . .
C7 C 0.8099(5) 0.1866(3) 0.5601(2) 0.0533(9) Uani 1 1 d . . . . .
H7 H 0.8076 0.1149 0.5811 0.064 Uiso 1 1 calc R U . . .
C8 C 0.7885(5) 0.2883(3) 0.5978(2) 0.0536(10) Uani 1 1 d . . . . .
H8 H 0.7690 0.2961 0.6484 0.064 Uiso 1 1 calc R U . . .
C9 C 0.3256(5) 0.3594(3) 0.36550(19) 0.0436(8) Uani 1 1 d . . . . .
C10 C 0.2263(5) 0.4106(3) 0.30016(18) 0.0427(8) Uani 1 1 d . . . . .
C11 C 0.3099(6) 0.5010(3) 0.26395(19) 0.0504(9) Uani 1 1 d . . . . .
H11 H 0.4418 0.5260 0.2808 0.060 Uiso 1 1 calc R U . . .
C12 C 0.2075(7) 0.5580(3) 0.2028(2) 0.0582(10) Uani 1 1 d . . . . .
H12 H 0.2714 0.6193 0.1814 0.070 Uiso 1 1 calc R U . . .
C13 C 0.0161(7) 0.5234(3) 0.1753(2) 0.0606(11) Uani 1 1 d . . . . .
H13 H -0.0527 0.5609 0.1355 0.073 Uiso 1 1 calc R U . . .
C14 C -0.0756(6) 0.4301(3) 0.20796(18) 0.0485(9) Uani 1 1 d . . . . .
C15 C 0.0277(5) 0.3729(3) 0.26991(17) 0.0413(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe C1 1.761(4) . ?
Fe C2 1.763(4) . ?
Fe C3 1.917(3) . ?
Fe C8 2.090(3) . ?
Fe C7 2.094(3) . ?
Fe C6 2.097(4) . ?
Fe C4 2.098(3) . ?
Fe C5 2.109(4) . ?
S N2 1.598(4) . ?
S N1 1.609(3) . ?
O1 C1 1.144(4) . ?
O2 C2 1.145(4) . ?
N1 C15 1.347(4) . ?
N2 C14 1.358(5) . ?
C3 C9 1.208(4) . ?
C4 C5 1.396(5) . ?
C4 C8 1.420(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.418(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.394(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.434(4) . ?
C10 C11 1.380(5) . ?
C10 C15 1.426(5) . ?
C11 C12 1.416(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.399(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.430(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Fe C2 95.16(15) . . ?
C1 Fe C3 88.80(15) . . ?
C2 Fe C3 89.56(14) . . ?
C1 Fe C8 120.95(15) . . ?
C2 Fe C8 93.38(15) . . ?
C3 Fe C8 149.61(15) . . ?
C1 Fe C7 94.26(15) . . ?
C2 Fe C7 126.43(16) . . ?
C3 Fe C7 143.26(16) . . ?
C8 Fe C7 38.93(14) . . ?
C1 Fe C6 102.63(15) . . ?
C2 Fe C6 157.61(15) . . ?
C3 Fe C6 104.15(15) . . ?
C8 Fe C6 65.85(15) . . ?
C7 Fe C6 39.53(15) . . ?
C1 Fe C4 159.56(15) . . ?
C2 Fe C4 92.94(15) . . ?
C3 Fe C4 110.02(15) . . ?
C8 Fe C4 39.65(14) . . ?
C7 Fe C4 65.98(15) . . ?
C6 Fe C4 65.91(15) . . ?
C1 Fe C5 138.92(16) . . ?
C2 Fe C5 125.79(15) . . ?
C3 Fe C5 88.44(14) . . ?
C8 Fe C5 65.48(15) . . ?
C7 Fe C5 65.67(15) . . ?
C6 Fe C5 39.22(14) . . ?
C4 Fe C5 38.76(14) . . ?
N2 S N1 101.44(17) . . ?
C15 N1 S 106.1(2) . . ?
C14 N2 S 106.6(3) . . ?
O1 C1 Fe 178.8(3) . . ?
O2 C2 Fe 177.9(3) . . ?
C9 C3 Fe 178.6(3) . . ?
C5 C4 C8 107.4(3) . . ?
C5 C4 Fe 71.0(2) . . ?
C8 C4 Fe 69.85(19) . . ?
C5 C4 H4 126.3 . . ?
C8 C4 H4 126.3 . . ?
Fe C4 H4 124.5 . . ?
C4 C5 C6 108.7(3) . . ?
C4 C5 Fe 70.2(2) . . ?
C6 C5 Fe 70.0(2) . . ?
C4 C5 H5 125.6 . . ?
C6 C5 H5 125.6 . . ?
Fe C5 H5 125.8 . . ?
C5 C6 C7 107.3(3) . . ?
C5 C6 Fe 70.8(2) . . ?
C7 C6 Fe 70.1(2) . . ?
C5 C6 H6 126.3 . . ?
C7 C6 H6 126.3 . . ?
Fe C6 H6 124.3 . . ?
C8 C7 C6 108.1(3) . . ?
C8 C7 Fe 70.36(19) . . ?
C6 C7 Fe 70.3(2) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
Fe C7 H7 124.9 . . ?
C7 C8 C4 108.4(3) . . ?
C7 C8 Fe 70.71(19) . . ?
C4 C8 Fe 70.50(19) . . ?
C7 C8 H8 125.8 . . ?
C4 C8 H8 125.8 . . ?
Fe C8 H8 124.6 . . ?
C3 C9 C10 174.6(4) . . ?
C11 C10 C15 115.5(3) . . ?
C11 C10 C9 123.2(3) . . ?
C15 C10 C9 121.3(3) . . ?
C10 C11 C12 124.1(4) . . ?
C10 C11 H11 117.9 . . ?
C12 C11 H11 117.9 . . ?
C13 C12 C11 120.1(4) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 118.8(3) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
N2 C14 C13 126.7(3) . . ?
N2 C14 C15 112.3(4) . . ?
C13 C14 C15 120.9(3) . . ?
N1 C15 C10 126.1(3) . . ?
N1 C15 C14 113.4(3) . . ?
C10 C15 C14 120.5(3) . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.062

